OA12976A - Pyrrolopyrimidine derivatives. - Google Patents

Pyrrolopyrimidine derivatives. Download PDF

Info

Publication number: OA12976A
Authority: OA; OAPI
Prior art keywords: phenyl; amino; pyrrolo; pyrimidine; carbonyl
Prior art date: 2002-12-19

Application number

OA1200500187A

Other languages

English (en)

Inventor

Joel Thomas Arcari

Jinshan Chen

Susan Lagreca

Matthew Arnold Marx

Matthew David Wessel

Original Assignee

Pfizer Prod Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-12-19

Filing date

2003-12-08

Publication date

2006-10-13

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32682064&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=OA12976(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2003-12-08 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-10-13 Publication of OA12976A publication Critical patent/OA12976A/en

Links

150000004944 pyrrolopyrimidines Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 305
238000000034 method Methods 0.000 claims abstract description 167
229940002612 prodrug Drugs 0.000 claims abstract description 41
239000000651 prodrug Substances 0.000 claims abstract description 41
241000124008 Mammalia Species 0.000 claims abstract description 24
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
230000003463 hyperproliferative effect Effects 0.000 claims abstract description 11
239000004202 carbamide Substances 0.000 claims description 108
125000000217 alkyl group Chemical group 0.000 claims description 93
125000005843 halogen group Chemical group 0.000 claims description 57
125000003118 aryl group Chemical group 0.000 claims description 55
125000000623 heterocyclic group Chemical group 0.000 claims description 46
-1 anti- métabolites Substances 0.000 claims description 42
206010028980 Neoplasm Diseases 0.000 claims description 39
239000003112 inhibitor Substances 0.000 claims description 32
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
125000004093 cyano group Chemical group *C#N 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 26
201000011510 cancer Diseases 0.000 claims description 25
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 23
230000002159 abnormal effect Effects 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
230000010261 cell growth Effects 0.000 claims description 19
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 17
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
125000002252 acyl group Chemical group 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 13
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
102000004190 Enzymes Human genes 0.000 claims description 12
108090000790 Enzymes Proteins 0.000 claims description 12
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 11
230000012010 growth Effects 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
239000003102 growth factor Substances 0.000 claims description 8
VFCRSIORGUNNGT-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(2,4-dichlorophenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC=C(Cl)C=C1Cl VFCRSIORGUNNGT-UHFFFAOYSA-N 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000004404 heteroalkyl group Chemical group 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
239000004037 angiogenesis inhibitor Substances 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
JIJYZDRUGWAJLR-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-methoxy-5-methylphenyl)urea Chemical compound COC1=CC=C(C)C=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 JIJYZDRUGWAJLR-UHFFFAOYSA-N 0.000 claims description 4
OKIYGPJGNGRUON-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-propan-2-ylphenyl)urea Chemical compound CC(C)C1=CC=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 OKIYGPJGNGRUON-UHFFFAOYSA-N 0.000 claims description 4
LVKYWGHBTMCTGO-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-fluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(F)=C1 LVKYWGHBTMCTGO-UHFFFAOYSA-N 0.000 claims description 4
LMPLJSJKSQJGEE-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 LMPLJSJKSQJGEE-UHFFFAOYSA-N 0.000 claims description 4
QRWBSACLFSVZEF-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-ethoxyphenyl)urea Chemical compound C1=CC(OCC)=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 QRWBSACLFSVZEF-UHFFFAOYSA-N 0.000 claims description 4
FTTLMJBTSSQACU-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-propan-2-ylphenyl)urea Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 FTTLMJBTSSQACU-UHFFFAOYSA-N 0.000 claims description 4
UCQIBRXGBNSFKA-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(5-fluoro-2-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(F)=CC=C1C UCQIBRXGBNSFKA-UHFFFAOYSA-N 0.000 claims description 4
CIFHHRMGJLNMEQ-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC(C)=CC=C1F CIFHHRMGJLNMEQ-UHFFFAOYSA-N 0.000 claims description 4
GYOBORHBLFKMOX-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(3,5-difluorophenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC(F)=CC(F)=C1 GYOBORHBLFKMOX-UHFFFAOYSA-N 0.000 claims description 4
229940123587 Cell cycle inhibitor Drugs 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 4
230000002280 anti-androgenic effect Effects 0.000 claims description 4
230000003388 anti-hormonal effect Effects 0.000 claims description 4
239000000051 antiandrogen Substances 0.000 claims description 4
229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims description 4
WHMQOZBSVULDGM-UHFFFAOYSA-N methyl 4-[[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 WHMQOZBSVULDGM-UHFFFAOYSA-N 0.000 claims description 4
BNOXPWUUMZUSJJ-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-chlorophenyl]-3-chloro-4-methylbenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1Cl)=CC=CC=1NS(=O)(=O)C1=CC=C(C)C(Cl)=C1 BNOXPWUUMZUSJJ-UHFFFAOYSA-N 0.000 claims description 4
OKWYOZTUNJGJTJ-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-chloro-4-fluorobenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1C)=CC=CC=1NS(=O)(=O)C1=CC=C(F)C(Cl)=C1 OKWYOZTUNJGJTJ-UHFFFAOYSA-N 0.000 claims description 4
PZQISBSZHDGVDJ-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-2,4-dichloro-5-methylbenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC(C)=C(Cl)C=C1Cl PZQISBSZHDGVDJ-UHFFFAOYSA-N 0.000 claims description 4
LENJRZSMTWEGHS-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-4-butoxybenzenesulfonamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 LENJRZSMTWEGHS-UHFFFAOYSA-N 0.000 claims description 4
BALVVIKBOOKCQS-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-5-chloro-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 BALVVIKBOOKCQS-UHFFFAOYSA-N 0.000 claims description 4
JPEDMDMNODQZIV-UHFFFAOYSA-N n-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-fluorophenyl]-2,4-dichlorobenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(F)C=1NS(=O)(=O)C1=CC=C(Cl)C=C1Cl JPEDMDMNODQZIV-UHFFFAOYSA-N 0.000 claims description 4
YSCYVUYHNGFVMD-UHFFFAOYSA-N n-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-2-chloro-4-fluorobenzenesulfonamide Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NS(=O)(=O)C1=CC=C(F)C=C1Cl YSCYVUYHNGFVMD-UHFFFAOYSA-N 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
ANHIVJBWMLUKHH-UHFFFAOYSA-N (3-aminophenyl)-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidin-5-yl)methanone Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C1=CC=CC(N)=C1 ANHIVJBWMLUKHH-UHFFFAOYSA-N 0.000 claims description 3
PLODYPCIUFWXSN-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-4-chlorophenyl]-3-(4-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C(=CC=1)Cl)=CC=1NC(=O)NC1=CC=C(Cl)C=C1 PLODYPCIUFWXSN-UHFFFAOYSA-N 0.000 claims description 3
XEAZAZGALAURME-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2,5-difluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(F)=CC=C1F XEAZAZGALAURME-UHFFFAOYSA-N 0.000 claims description 3
VKCTUAXXHDUJDB-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 VKCTUAXXHDUJDB-UHFFFAOYSA-N 0.000 claims description 3
QLYNTQDQIVHXTE-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3,4-dimethylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C)C(C)=C1 QLYNTQDQIVHXTE-UHFFFAOYSA-N 0.000 claims description 3
RPHMAQJLRVWQLQ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(Cl)=C1 RPHMAQJLRVWQLQ-UHFFFAOYSA-N 0.000 claims description 3
MRILIBUNFXYMJN-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-cyanophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(C#N)=C1 MRILIBUNFXYMJN-UHFFFAOYSA-N 0.000 claims description 3
NNZKAYJSMIOWLC-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-fluoro-4-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C)C(F)=C1 NNZKAYJSMIOWLC-UHFFFAOYSA-N 0.000 claims description 3
JUVPBXIDIGBFKY-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(C)=C1 JUVPBXIDIGBFKY-UHFFFAOYSA-N 0.000 claims description 3
ADPWOQHEGMITGH-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-chloro-2-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C=C1C ADPWOQHEGMITGH-UHFFFAOYSA-N 0.000 claims description 3
BAABCALYOOIAEM-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C=C1 BAABCALYOOIAEM-UHFFFAOYSA-N 0.000 claims description 3
GTYWJSQMWRYEOY-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-fluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(F)C=C1 GTYWJSQMWRYEOY-UHFFFAOYSA-N 0.000 claims description 3
WRDBKJMACQYBFZ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C)C=C1 WRDBKJMACQYBFZ-UHFFFAOYSA-N 0.000 claims description 3
SJJZDMLQNNOAJO-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 SJJZDMLQNNOAJO-UHFFFAOYSA-N 0.000 claims description 3
VEZCJYLOEWLZNM-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-cyclohexylurea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1CCCCC1 VEZCJYLOEWLZNM-UHFFFAOYSA-N 0.000 claims description 3
ZIIUTFLNEYPNIZ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 ZIIUTFLNEYPNIZ-UHFFFAOYSA-N 0.000 claims description 3
SUQWIWWBMQLMER-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-chlorophenyl]-3-(3,5-dichlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(Cl)C=1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 SUQWIWWBMQLMER-UHFFFAOYSA-N 0.000 claims description 3
KURTXTCSRFPGBN-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-fluorophenyl]-3-(2-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC=C1Cl KURTXTCSRFPGBN-UHFFFAOYSA-N 0.000 claims description 3
WOBPWTKMWKMHSJ-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(2-chlorophenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC=CC=C1Cl WOBPWTKMWKMHSJ-UHFFFAOYSA-N 0.000 claims description 3
GQIANKOKVCCNQL-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(3,5-dichlorophenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 GQIANKOKVCCNQL-UHFFFAOYSA-N 0.000 claims description 3
OPSIYOLKNZFXRY-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(3-cyanophenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC=CC(C#N)=C1 OPSIYOLKNZFXRY-UHFFFAOYSA-N 0.000 claims description 3
VUZYXRDZUGCHNQ-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(3-fluoro-4-methylphenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC=C(C)C(F)=C1 VUZYXRDZUGCHNQ-UHFFFAOYSA-N 0.000 claims description 3
MGFHAMRNPOLMJC-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-(3,5-dichlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(C)C=1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 MGFHAMRNPOLMJC-UHFFFAOYSA-N 0.000 claims description 3
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SGDBOTFOCXARCG-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-(3-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(C)C=1NC(=O)NC1=CC=CC(C)=C1 SGDBOTFOCXARCG-UHFFFAOYSA-N 0.000 claims description 3
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Classifications

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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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2003
- 2003-08-12 UA UAA200506094A patent/UA80171C2/uk unknown
- 2003-12-08 KR KR1020077015815A patent/KR20070087020A/ko not_active Withdrawn
- 2003-12-08 WO PCT/IB2003/005841 patent/WO2004056830A1/fr not_active Ceased
- 2003-12-08 ES ES03777060T patent/ES2364649T3/es not_active Expired - Lifetime
- 2003-12-08 AU AU2003286317A patent/AU2003286317A1/en not_active Abandoned
- 2003-12-08 AP AP2005003342A patent/AP2005003342A0/xx unknown
- 2003-12-08 BR BR0317524-3A patent/BR0317524A/pt not_active IP Right Cessation
- 2003-12-08 JP JP2004561818A patent/JP4057013B2/ja not_active Expired - Fee Related
- 2003-12-08 MX MXPA05006793A patent/MXPA05006793A/es not_active Application Discontinuation
- 2003-12-08 PL PL377774A patent/PL377774A1/pl not_active Application Discontinuation
- 2003-12-08 OA OA1200500187A patent/OA12976A/en unknown
- 2003-12-08 CA CA002510853A patent/CA2510853C/fr not_active Expired - Fee Related
- 2003-12-08 CN CNA2003801064513A patent/CN1726218A/zh active Pending
- 2003-12-08 EP EP03777060A patent/EP1578751B1/fr not_active Expired - Lifetime
- 2003-12-08 KR KR1020057011297A patent/KR20050084402A/ko not_active Ceased
- 2003-12-08 RS YUP-2005/0469A patent/RS20050469A/sr unknown
- 2003-12-08 AT AT03777060T patent/ATE512965T1/de not_active IP Right Cessation
- 2003-12-08 HR HR20050560A patent/HRP20050560A2/hr not_active Application Discontinuation
- 2003-12-08 EA EA200500814A patent/EA200500814A1/ru unknown
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- 2003-12-17 GT GT200300289A patent/GT200300289A/es unknown
- 2003-12-18 TW TW092135947A patent/TW200423939A/zh unknown
- 2003-12-18 NL NL1025068A patent/NL1025068C2/nl not_active IP Right Cessation
2005
- 2005-05-30 IS IS7872A patent/IS7872A/is unknown
- 2005-05-31 ZA ZA200504440A patent/ZA200504440B/en unknown
- 2005-06-09 NO NO20052802A patent/NO20052802L/no not_active Application Discontinuation
- 2005-06-17 TN TNP2005000165A patent/TNSN05165A1/fr unknown
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Also Published As

Publication number	Publication date
IS7872A (is)	2005-05-30
ZA200504440B (en)	2006-07-26
ATE512965T1 (de)	2011-07-15
US7271262B2 (en)	2007-09-18
EP1578751B1 (fr)	2011-06-15
NL1025068A1 (nl)	2004-06-22
PL377774A1 (pl)	2006-02-20
AR042509A1 (es)	2005-06-22
ES2364649T3 (es)	2011-09-08
PA8591701A1 (es)	2005-05-24
CA2510853C (fr)	2009-04-28
GT200300289A (es)	2004-09-21
MA27568A1 (fr)	2005-10-03
TNSN05165A1 (fr)	2007-05-14
NO20052802L (no)	2005-07-19
HN2003000416A (es)	2006-07-25
NO20052802D0 (no)	2005-06-09
MXPA05006793A (es)	2005-09-08
AP2005003342A0 (en)	2005-06-30
US20050037999A1 (en)	2005-02-17
CN1726218A (zh)	2006-01-25
PE20040914A1 (es)	2005-01-08
KR20070087020A (ko)	2007-08-27
ECSP055867A (es)	2005-09-20
BR0317524A (pt)	2005-11-16
CA2510853A1 (fr)	2004-07-08
NZ540456A (en)	2007-11-30
EA200500814A1 (ru)	2006-02-24
WO2004056830A1 (fr)	2004-07-08
JP4057013B2 (ja)	2008-03-05
TW200423939A (en)	2004-11-16
RS20050469A (sr)	2007-11-15
AU2003286317A1 (en)	2004-07-14
EP1578751A1 (fr)	2005-09-28
JP2006512356A (ja)	2006-04-13
UA80171C2 (en)	2007-08-27
KR20050084402A (ko)	2005-08-26
HRP20050560A2 (en)	2006-02-28
NL1025068C2 (nl)	2004-11-16
UY28132A1 (es)	2004-07-30

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